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Ep. 268: How This Bougie Backpacker Travels the World as a Remote Freelancer with Leah Arao

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In this episode, I speak with Leah, a bougie backpacker who lives for slow travel, finding the best coffee shops to work from and rooftops for you in each city she visits. 

As co-creator and co-host of the Ticket 2 Anywhere podcast, she motivates others to seek adventures from anywhere. 

By trade, she is a podcast producer, MC/host, plus an event and community manager and frequently takes her work on the road from her home base in Los Angeles.

Listen on to find out how this bougie backpacker travels the world as a remote freelancer. 


Listen below:

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Transcription:

Debbie:

Hey everyone. Thank you so much for being here. 

I am really excited to speak with my guest today. I’m here with Leah. 

Hey Leah, how are you?

Leah:

I’m good, Debbie.

It’s so good to be chatting with you again.

I know we’ve recently had you on our podcast Ticket 2 Anywhere, and then you and I used to co-host some clubhouse rooms on podcasting in 2021. So we got to chat almost every week.

Debbie:

I know it’s so weird that we’re not talking to each other every single week anymore. And I did miss our chats together. And sometimes there would be nobody in the room except me and you. And we’re just like, okay, well just talk about what we did this week and

Leah:

Catch up on life. Yeah.

Debbie:

And then sometimes I’m like, oh, there’s other people in the room. Now we have to talk about other stuff.

Leah:

Now we actually have to do our clubhouse job. Yeah. I remember those days.

Debbie:

I was like, this sucks anyways, but yeah. Thank you so much for being here, Leah, can you tell us about you and why you live an offbeat life?

Leah:

Oh, a hundred percent. I love this question. I hear it every time on your podcast. 

I am Leah also known as LA and flight. I am by trade and event manager and a podcast consultant. 

And by life, you know, I’m a slow traveler, bougie, backpacker. 

I love talking about coffee shops and rooftops with my friends, my audience and anyone else on the interwebs, right? Offbeat life, I just, I feel that the past seven years I’ve really shaped my life into what I want it to be by finding the right roles for me, roles that fit into my life that allow me to live freely. As it allows me to have enough money to live abroad, to travel. 

I, luckily, you know, don’t have any commitments tying me down. I know that’s very different from, for everyone. And I live a very privileged life by being able to say this, but, you know, I’ve morphed it into more of, okay, how can I make this better for myself?

And, you know, still, come back for family and friends back to my home base of LA when I can. So I feel that I live a very flexible and dynamic life, which is what makes it offbeat.

Debbie:

I love that. And you know, what’s really funny is a lot of people think that you need to have a ton of money to be able to do this. And we’re really lucky to be living in a time where you have all of this flexibility because of remote work, because you can work on the road while before that was pretty much impossible, right? And it is still fairly new to do this, but you are able to do this yourself and you have two jobs. 

Can you tell us more about that and how you’re able to sustain this? Cause this is pretty incredible.

Leah:

Gosh, well, it’s two, luckily it’s two part-time roles, which is great, which equals one full-time life gig, but one of them is in podcast management slash events, one client uses me for both of my strengths. And then that is like a contractor role. 

So when we’re doing taxes it’s 10 99, right? And the other company is a very large energy drink company with whom I have a great relationship with. And I contract with them frequently on and off for the past four or five years. And with them, I’m actually a W2 and hired through an agency. 

And so it’s really easy with them and how I separate yet keep these both in check is that I absolutely have to time block my schedule and stick to the time block. And it’s very articulate planning when it comes to being able to if one role has to take over like a whole week, if I’m doing a week long event, I have to let the other know in advance.

Like, hey, you know, I need this time off essentially. So it takes a lot of articulate planning, looking at the calendar constantly, like twice, at least twice a day to be like, okay, has anything changed in the next few weeks? Do I need to like, alert one about the other? You know? But I am very, very blessed. Like there’s a lot of people that are just looking for one role right now. 

So, the fact that I have two, because I’ve created these great relationships, I purposely created these great relationships for myself. You know, I’m very happy about that.

Debbie:

Yeah. So let’s talk about that because like you had mentioned, a lot of people don’t have these types of opportunities and you do, and they’re two very different roles, like as a podcast manager and as an event manager, and that’s not necessarily, I mean, it’s not too far off, but it’s not too close together that you’re like, oh, it makes sense. 

How did you decide to do this type of work for yourself? Was this something that you knew you wanted to do or you kind of created these opportunities for yourself?

Leah:

So, I actually love this kind of origin story because I worked in media and advertising for the first five years of my career, and I was living in Las Vegas and Los Angeles and, you know, very corporate, climbing up the corporate ladder. 

I realized it was not for me. So, I went off to South America when, you know, the department got dissolved when I lived in Las Vegas for that company. 

So I said, “okay, now is my time to travel.”. Went to backpack in South America for a year. Then I went to live in Australia, a working holiday visa for a year. 

And that is actually where I pivoted my career to event management. And I was already doing it pro bono with, you know, different community organizations while I was working my full-time job previously. But I said, you know, maybe it is time to get paid for doing what I love.

And the only reason I was able to do that is because I had to take a step back from pay, right? Take a step back from pay, take a step back from title and really say, “well, this is what I wanna do, this is what I wanna excel in. So, I’m just gonna go down this path”, but it was still a livable wage as Australia does. Right? Cause that was that’s, that’s one of my claims to fame. I was able to pivot my career in another country, like who can actually do that. Right? Yeah, so I did that for a few years and that, and I, I loved it. 

I sell my event management services to whoever I can, whatever is a good fit. Whoever I wanna work with. And at the beginning of the pandemic events went down, right? I said, “uh-oh, what am I gonna do?”.

And I was already managing my podcast and I loved it so much. And I believed it so much. I said, “well, why can’t I, I partner with others to help them launch theirs or give them advice on theirs or manage theirs.”. 

So, I was able to, to kind of sell those services to, to other folks. And yeah, that’s how I became a podcast manager. I had to realize that I’m like, “okay, I need more, I need to diversify my skill set.”, because what happened in March 2020 affected a lot of us. And I can’t, you can’t just kind of just depend on one stream of income or one set of skills. 

And I do realize that’s, that’s also very privileged to say, but I’m, I’m glad I was able to pivot that as well. There’s a lot of folks that aren’t able to, or they have others to support. And luckily I could just focus my time and energy on myself. So I did.

Debbie:

But I do have to say pivoting and changing gears and also working with what you have is also really hard. And it is something that a lot of people have a problem with because,

Leah:

Mm-hmm.

Debbie:

most of the time you have these dreams and these goals that you have, but then if you don’t take action, it’s never going to happen. Right? So, it is a privilege, but also it is also work on your part that you had to do because you wouldn’t have gotten these opportunities if you didn’t go out there and try to get them. 

So, I do have to kind of say it is, but it isn’t because I’ve seen too many people say they want this, but they never actually go out there and do something about it. 

So, talking about that, Leah, you did not go to school for any of these things that you’re trying to do. 

You didn’t go to podcasting school, you didn’t go to event planning school. You created all of these opportunities for yourself. 

How did you actually get from somebody who was doing things pro bono and for yourself to making this into an income creating job for yourself?

Leah:

I would say the biggest is you have to start, and this is you have to start pro bono, to be honest. And you have to smart start at the smaller opportunities. Sorry, I have so many thoughts coming in at once that I wanna say five things at once. 

You have to start with a smaller opportunity, you have to start pro bono, but it’s the same, it’s the same path that I’m going through now with being a content creator, a travel content creator on the side, right? Where we eventually, that’s how we want all the income to come in. But, before I can get paid for things, you have to do the gifted collabs and you have to do them well. Right? So, that’s kind of what I’m going through there. 

Whereas in my professional life, as an event manager and podcast manager. Yeah, with events, like I said, in Australia, I had to take a step back in order to find a role that fits.

However, I was doing events pro bono for five years. So, absolutely put that on your resume and absolutely talk about what you handled because volunteer experience is still experience. And I’ve noticed nowadays that jobs on like LinkedIn, when I’m looking through, cause you should always be looking right. There’s no harm in looking, but the jobs are always, it’s true. And like you don’t ever know what’s gonna happen to the world next. Right? So, the jobs are like, “oh, we want five years of non internship or non volunteer experience”. 

Debbie:

Mm-Hmm.

Leah:

So, I’m noticing that I do that because back in like, you know, 2017, I was like, “oh yeah, I’ve done events before like six years of work experience”. I didn’t tell them that it was like five years of unpaid volunteer or unpaid event experience. But I still got hired because I was able to demonstrate that yeah, I’ve led successful events where people paid and attended and you know, the customer satisfaction score was great.

So, you’re right. I didn’t go to event planning school. I majored in marketing and I minored in Spanish when I went to university. And as far as pivoting my career to podcast, that one, I mean, podcasting, as you know, Debbie, like you have whole courses on it. It’s just the wild, wild west right now in the past few years. And I kind of like that. So, it’s a good time to get in. Like, they’re not necessarily regulated; a platform can kick you off if they don’t like your show, but it’s, they’re not regulated by the same bodies that regulate movies and commercials, et cetera. 

And people are still trying to figure out what the hierarchy is like, how to sell space. 

People are trying to figure out roles for themselves. So, I can call myself, podcast producer, but I don’t touch the editing. Right? Like Trizzi and I on our show, we’re both producers, but I’m out here doing a lot of the marketing, helping to book guests like writing scripts for the show, shaping the interviews, et cetera. It’s different, but being able to help others, the way I got into that was just again, starting small. Like, I’m still on Upwork and I’ve made a name for myself on Upwork, which I am glad I have, but you know, maybe taking those jobs to build up your portfolio.

Debbie:

Yeah. And I, I do again, wanna emphasize the fact that you don’t necessarily need to get paid for something in order to have experience in it. And I,

Leah:

Mm-hmm.

Debbie:

absolutely 100% agree with that because a lot of the things that I have done, you know, whether this podcast or my website, I’ve gotten jobs from it and I didn’t go to school for it. And I think that’s one of the things that people usually are very afraid of. Like, you know, I don’t have paid experience or I didn’t go to school for this. Or even though I really love this, I’ve done it a few times. I wanna keep going. I’m just too afraid to do it because of X, Y, and Z. And we both can attest the fact that you don’t need corporate or whatever schooling or anything like that to actually be hired.

If you know what you’re doing and you’re doing it well, if you go in an interview, they were, they’re going to see that because they’re, you’re gonna be able to express all of the things that, you know, your knowledge about the industry and what you’ve done as well. And if you can get references from the people that you’ve worked for, it’s not as hard as you think if you actually know what you’re doing. 

So, I actually really love that you were able to do this Leah, because I’m that type of person too, where I’m just like, you don’t need education. Like real life education is somewhat, I mean, I think for me more valuable than, than schooling because you can’t really take things off the books and then, you know, it’s, it’s a lot different than real life.

Leah:

Yeah. And what I think a lot of com- or what I would hope a lot of companies look for is not only your experience, but they look for basically people who are coachable and people who have a growth mindset and are quick to learn. Right? 

And I know everyone uses that like quick to learn, but how dynamic can you be when there’s change? When you have to adapt, how good are you at receiving feedback and taking that, turn it into action? Right? And that is one of my best qualities. I’m so proud of that. I’ve heard that I’m coachable. I’ve heard that I’m dynamic. So I use that. 

I mean, after what, seven, eight years of a career, now, I use that as my, my lead in my resume. I say, “Hey, like I’m dynamic, I’m coachable. Just talk to have one interview with me and you’ll see”, you know? So, and, I do well on the teams that I’m on. So, I think that being able to, to adapt and shift is a big quality that a lot of companies, business owners, et cetera, look for in people they want to work with, which is how I was able to get, you know, the roles that I do.

Debbie:

Yeah. And that’s a huge thing. And now you have this lifestyle that you can literally take with you anywhere in your remote,

Leah:

Mm-hmm.

Debbie:

and you enjoy what you do. So how has your life changed? Because most of the time, when we grew up, it was like, okay, we travel when we have vacation time off,

Leah:

Mm-hmm.

Debbie:

and time off, not travel while we’re working. So how has that changed the way you live your life and how you kind of schedule your way around things because it’s completely different.

Leah:

Mm-hmm, well, luckily the role that I help with events and podcasts with they’re fully remote forever, always. So, they have never been in person, they’ve always been online, which is great. And then the other company that I have, like, you know, more W2 short term contractor with the department I’m with, and the team I’m on is so incredibly flexible, which I learned recently is not very common there. And I’m like, how, like everyone knows this brand in the public eye is like a really cool laid back brand. But I think it’s just certain teams, right? So I do events and trainings within HR there. So, the talent team slash HR, they’re pretty flex. And I think it involves a lot of communication, keeping track of your calendar, talking with your team on what’s expected as far as, you know, remote work obviously. 

And so I think, I also think within that company, I just got really lucky with my team that doesn’t expect all of us to be in all the time, but I definitely try to over communicate and say, “Hey, you know, I’m not gonna be online until this time.”. Like I set those, I set these boundaries where I’m like, I’m not gonna be online until this time. And like I said, I’m not full time with them either. So they get it, right? All that being said, both roles being as flexible as they can. I definitely take advantage of it. And you know, like one of my core pillars of being a travel content creator is like scoping out amazing coffee shops around the world. So, I love to work remotely from them anyway, because I believe coffee fosters community. It’s a big pillar of the community wherever you are. And I just love, I love coffee culture. I love cafe culture. So, I’m always trying to explore it wherever I am. So, that goes hand in hand with me working from there. Like, “oh, just bust out my laptop.”.

Debbie:

And I love whenever I look at Leah’s social media, especially on Instagram, she’s always going to new and different places, which is always so exciting. 

And you’re showcasing all of these spots. So, how has it changed for you since the pandemic? Are you starting to travel now? Things are starting to open up,

Leah:

Mm-hmm. 

Debbie:

and like, are you going anywhere, like super exotic that we would like to kind of go with you?

Leah:

Oh my, yes, I am. I’m actually, one of the biggest things I’d say overall as a traveler, as LA in Flight, right? Is that I used to be super like budget, budget. Like, even though it was in my late twenties, like a budget backpacker, 18 year olds, not style, but like traveling as cheaply as I could. And I notice, I think not only does your style, travel style evolve as you age, but with an event like the pandemic where I didn’t travel for almost, actually, I did in October 2020, I did go to Mexico for a bachelorette party. If it was like a weekend away, I wouldn’t have gone, but it was a big life event, you know? So, we went, but then after that, I didn’t travel for almost another year until like July 2021. So, all of this time of working and saving and being able to shift my finances around, like really kind of put me in the flash packing slash bougie backpacking bracket, it kind of bumped me up.

Leah:

And I was like, well, I don’t have to be as penny pinching as I was before. Not only due to finances, but I think looking at the way the world was, I was like, “okay, well, do I want a private room in a hostel versus a shared dorm with 20 people where I could possibly get sick?”. Right? And that’s stuff we weren’t worried about in the past, but I think everything that’s been happening in the past few years, it’s like, kind of forced us to look at health a little differently, public health, a little differently. 

So, you know, it’s like, do, I would rather pay $10 extra night, to have that peace of mind knowing that there’s not gonna be people in and out of my space, it’s just gonna be me and I can deep clean or sanitize it and be as far away from people as I want.

Right? So things like that. Or just if I wanted a better night’s sleep, like I’m like, “okay, it was a lot of, now it’s a lot of, “Ooh, do I wanna stay in a three star, three or four star hotel?”. 

I’m not a luxury traveler, yet. So, you know, maybe someday, but like, I’m like, “Ooh, do I wanna stay in, like a nice little cute boutique hotel versus a hostel where it’s like loud and crazy all the time?”. Even though that’s what I do. 

Like, I love meeting people on the road. I think my style has changed a bit, right? I’m like, I can still go party, but then I wanna come home to the peace and quiet, right? 

And I’ve noticed the past few years, a lot of different types of stay accommodation have been popping up. Co-Working accommodation, co-living accommodation, like service department type of accommodation.

It’s not just hotels, Airbnbs, hostels, anymore, home stays. It’s not just like those four huge brackets. It’s like, oh, this is like a service department where everything you do is digital. And then you get there and you have your place. And we have a virtual concierge. Like, it’s so crazy how the travel world has evolved. 

I think it’s so cool. It’s very interesting. And it makes me excited for, you know, the industry, as I, as I’m seeing it unfold, there are sometimes where I don’t even talk to a human and everything’s done online. Our keys are on our phone, digital keys. And I’m like, this is kind of cool. You know, I hope it’s not displacing people from jobs, but, but I’m like, this is cool. This is the future, right? People want more contactless, maybe they don’t wanna interact as much, people want different things. And I think travel is evolving to tap everyone that wants a different thing.

Debbie:

Yeah. And it’s so true that we travel so differently. Like, I totally agree with you in my twenties, like I used to stay in hostels and now I’m like, “yeah, no, I’m, I feel too old for that now, I cannot do that. I need my own room.”, and like, “I need a nicer hotel. I can’t do this anymore.”, but it’s different, but I think it’s really important to be able to see that change within yourself and to travel in all those different types of ways, because you appreciate it so much more than if you just go one hundred percent, one way.

And that’s it, whether you’re bougie or your budget, it doesn’t matter. It’s like they all have their pros and cons in a lot of ways. Now, you did mention this, Leah that you do love to make friends with people and you’re an obvious extrovert and you, you travel quite often and you could take your work from anywhere. 

How do you create these connections with people when you are on the road? Because that’s really one of the hardest things, especially if you’re traveling solo or maybe traveling solo half of it, and then you kind of have to go on your own. 

If you don’t have friends or family that can remote travel and work with you, it’s kind of, a solo thing for the most part.

Leah:

Mm-hmm.

Yep. 100%. And I think with anything, anything in life, it’s a mindset shift at first, it is recognizing that because some people do want to travel alone, alone, alone. They don’t wanna talk to anybody, right?

But if you want to meet people, meet friends and just hear other peoples interesting stories on the roads. You have to put yourself in situations where that’s gonna happen. Right? There’s jokes like in the dating world about how it’s like, I want, you know, how am I gonna meet my husband? You stay at home all the time. Like literally no extracurriculars, no nothing, no out on the weekends, like nothing, you know, but you have to put yourself in situations where you’re going to meet others. So kind of think of what you, I would say to start and overall think of things you really are interested in or that you like to do.

Right? And this applies back home. 

Debbie:

Mm-Hmm.

Leah:

There are so many situations where I’ve moved back to LA back home and I’ve had to kind of start from scratch as far as social life, because I’ve been gone for so long or moved to a different part of LA. And I’m like, “okay, I really wanna get to know my neighborhood here. What can I do?”, right? 

So think of hobbies, things you really like to do, whether that’s, like volunteering, working out, you know, different things, helping others, exploring new restaurants, et cetera, and put yourself in those situations in order just to like start meeting new people, right? Then you can break the ice with them, gather the confidence to approach them and maybe start forming friendships and just people relationships that way. That’s the overview of it. 

And then keeping those, maintaining those, oh, that’s a whole different after part, because it’s all about consistency. Making sure that you show up, right? 

Showing up is half the battle. And then when I’ve met some of my best friends in other countries, it’s keeping in touch on different time zones, which is tough, but I always make it a point to do it. And so do my friends, you have to prioritize the friendships that you wanna keep. Right?

Debbie:

And especially now with the pandemic and everyone, even when your friends are close, they’re still far away.

Leah:

Mm-Hmm.

Debbie:

We do have the experience now of like, how do we keep in touch with our friends, even though like they’re close, but we can’t really see each other. And, you know, versus the friends that are far away. 

And it’s so funny when you do become lifelong friends with people that you’ve met all around the world and you always have the most interesting like meeting, you know? 

And when people ask you, like, how did you meet? And you’re like, well, we were in a mountain and, 

Leah:

I love, those are my favorite stories though.

Debbie:

They are, they’re the best.

Leah:

So random.

Debbie:

I know I had one friend that we literally met in bed. So when people ask it’s like, how do you,

Leah:

Oh my gosh!

Debbie:

Like how did you meet each other, in bed?

Leah:

In bed? Wait, please elaborate on that story. Like, what do you mean?

Debbie:

I actually interviewed her here on the podcast. We were on a press trip and we shared a room together and I got in late and I woke, I mean, I got into the room and she was in bed already. And then she was like, “oh, hey”, I was like, “hi, nice to meet you. I’m Debbie.”. She was like, “nice to meet you too.”. It was so funny. And then I woke up the next day and I told her, I’m like, “you know, this is gonna be a really interesting story when we tell people how we met and like, you know, we met in bed, we met in bed”.

Leah:

I love that. I really love that though.

Leah:

So yeah, the best way to meet…

Debbie:

Exactly.

Leah:

Yeah. Different. I love that.

Debbie:

So Leah, looking forward to around 30, to maybe even 50 years from now, and you’re looking back at your life, what legacy would you like to leave? And what do you wanna be remembered for?

Leah:

Ooh, this is, this is interesting. I don’t know that I wanna say I haven’t thought much about it yet. But, I definitely always want to be able to help people adventure from anywhere, which is the slogan of our podcast, Ticket 2 Anywhere. 

Throughout the past two years, we’ve had to also have another mindset shift of, to vacation and to travel and to have a getaway is not to go across, it doesn’t have to be going across the world every single time, right? 

Very lucky to live in Los Angeles where we live, where people vacation. So, being able to explore from our backyard, showing people how to slow travel, help them adventure from anywhere, but still being, being able to maintain my relationships and friendships back home with my family and my best friends. It sounds like I wanna be able to do it all, but really I just want to have the best relationships I can while being able to help others get out into the world as well.

Debbie:

I love that. And you know, when you can do it all the time, it’s, it’s even better. And I think it’s, really good that someone like you is spreading that because I think a lot of people believe that it’s impossible and I’ve seen single people do it, married people do it. People who have children, like everybody, could literally do this type of lifestyle. 

It’s just a matter of your preparation and how you actually go about it. That’s different. Right? And it’s, it can be doable for everybody and you don’t have to be a multimillionaire or making like,

Leah:

No way.

Debbie:

multiple six figures to do this. But if you prepare for it really well, it’s possible. 

So, but thank you so much, Leah, for being here with us, we really appreciate you for sharing your journey. 

If our listeners wanna know more about you, where can they find you?

Leah:

I am LA and Flight on every single social media platform you can imagine, the website is still in progress. I am also appearing twice a month or almost every day, at least on social media on ticket number two anywhere podcast. So, we’re a visual podcast. You can find us on YouTube and anywhere you can listen to podcasts.

Debbie:

Love it. Make sure you go ahead and listen to that. And we’ll obviously put all of the links on the episode, on our website as well. 

Thank you so much, Leah, for being here. We really appreciate you!

Leah:

Thank you so much, Debbie. This is so fun!

 


Listen to Leah’s extended interview where she talks about how to become a freelancer on Upwork.

What you’ll find:

In this extended interview, Leah talks about becoming a freelancer through the remote work platform, Upwork.


Follow Leah:


 

Show Credits:

Audio Engineer: Ben Smith

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